Triethylamine → HCID 69586491, compound

HRID 723214Notes

Reaction equation

HRID 723214 reaction equation
[CH3:1][O:2][C:3]([C:5]1[S:6][C:7]([S:23][CH3:24])=[C:8]([S:10]([C:13]2[CH:21]=[C:20]([Br:22])[C:16]3[N:17]=[CH:18][NH:19][C:15]=3[CH:14]=2)(=[O:12])=[O:11])[CH:9]=1)=[O:4].[C:25]1(B(O)O)[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.[N+]1([O-])C=CC=CC=1.C(N(CC)CC)C>C(Cl)Cl.CC([O-])=O.CC([O-])=O.[Cu+2]>[CH3:1][O:2][C:3]([C:5]1[S:6][C:7]([S:23][CH3:24])=[C:8]([S:10]([C:13]2[CH:21]=[C:20]([Br:22])[C:16]3[N:17]=[CH:18][N:19]([C:25]4[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=4)[C:15]=3[CH:14]=2)(=[O:11])=[O:12])[CH:9]=1)=[O:4]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 12753Pyridine N-OxideHCID 66827Phenylboronic AcidHCID 58700468HCID 58700468, compound

Product 1

HCID 69586491HCID 69586491, compoundYield 51.3%

Reagents, catalysts & solvents 2

HCID 8895Cupric acetateCatalystHCID 6344DichloromethaneSolvent2×

Procedure

4-(7-Bromo-3-phenyl-3H-benzoimidazole-5-sulfonyl)-5-methylsulfanyl-thiophene-2-carboxylic acid methyl ester was prepared according to literature (Lam, P. Y. S. et al., Tetrahedron Letters, 42:3415 (2001)) using 4-(7-bromo-3H-benzoimidazole-5-sulfonyl)-5-methylsulfanyl-thiophene-2-carboxylic acid methyl ester (20 mg, 44.7 μmol, Example 38: step e), phenylboronic acid (11.4 mg, 93.5 μmol), Cu(OAc)2 (8.5 mg, 46.8 μmol), pyridine N-oxide (4.7 mg, 49.2 μmol), triethylamine (13 μL, 93.3 μmol), and CH2Cl2 (1.5 mL) in a loosely-capped, 1-dram vial. The reaction mixture was diluted in CH2Cl2 and washed with water and brine. The organic layer was dried over magnesium sulfate. Removal of solvents in vacuo followed by preparative TLC afforded the title compound as a brown oil (12 mg, 51%). ESI-MS (m/z): Calcd. for C20H15N2O4S3: 522.9 (M+1); found: 525.0.

Workup

  1. custom4-(7-Bromo-3-phenyl-3H-benzoimidazole-5-sulfonyl)-5-methylsulfanyl-thiophene-2-carboxylic acid methyl ester was prepared
  2. washwashed with water and brine
  3. dry with materialThe organic layer was dried over magnesium sulfate
  4. customRemoval of solvents in vacuo

Sources & evidence

ORD record
ord-20ac347a1a4947d38db7a26510e213a2
Source dataset
uspto-grants-2006_11
Patent number
US07138530B2

Reaction notes

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